


Four Times Philip Hamilton Tried to Ask Theodosia Burr Out and the One Time He Succeeded

by JetGirl1832, tomatopudding



Series: The Hamilton Family Album [30]
Category: Hamilton - Miranda
Genre: Cute, Dating, F/M, Halloween, Hamilkids, Kid Fic, Middle School, Slow Burn, Summer, Summer Camp, practically glacial, slowest of slow burns
Language: English
Status: Completed
Published: 2016-03-18
Updated: 2016-04-15
Packaged: 2018-05-27 10:45:43
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 7,479
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6281503
Author URL: https://archiveofourown.org/users/JetGirl1832/pseuds/JetGirl1832, https://archiveofourown.org/users/tomatopudding/pseuds/tomatopudding
Summary: <blockquote class="userstuff">
              <p>Philip Hamilton has liked Theo for a very long time, and it's not that he hasn't tried to ask her out... He's just been thwarted at every turn. One day he'll get it right, he's sure of it.</p>
            </blockquote>





	1. Attempt #1

**Author's Note:**

> Here is the next piece in our Hamilton Family Album series! Enjoy your stay.

Philip Hamilton and Theo Burr had been friends for as long as he could remember, in fact he couldn't remember a time when they weren't friends. She was nearly as much a part of his life as his little sister Angie, but lately things had started to change between them. Philip didn't know how to explain the feelings he was beginning to have for his friend and knew that if he talked about it with any of his classmates they would certainly laugh at him.

Most of the other boys in his class were still at the point in their lives where they considered girls to be gross and full of cooties. Having spent so much time with Angie and Theo, Philip knew that this was definitely not the case.

Without able to talk to his friends Philip was stumped as to what to do. When he came home he was greeted by his mother, "Hi sweetie how was school today?"

Philip shrugged, "Okay, I guess."

He settled himself at the kitchen table and his mother placed his usual after-school snack in front of him. Philip propped his elbow on theta me and leaned his chin on his hand, staring down at the carrot sticks and ranch in front of him.

Philip tried to avoid eye contact with his mother. She kept giving him worried glances.

"Philip?" Eliza sat down beside him, "is something wrong?"

Philip shook his head.

Eliza watched him for a moment before reaching out to cup Philip's cheek.

"What is it, sweetheart?" she asked softly, "You can tell me."

Philip felt his face get warm, he bit at her lower lip, "It's Theo..." she spoke quietly.

"Oh?" Eliza smiled there was a hint of amusement in her voice.

Philip didn't really know how to say what he was thinking and simply chewed at his lip.

"Yes?" prompted Eliza gently.

"I uh..." Philip brushed his hair from his face, "I think I like her... I think I like her, like her."

"Oh, sweetheart, that's wonderful," Eliza said, "Are you going to tell her?"

Philip shrugged, "I dunno."

Eliza smiled and pressed a kiss to the top of her son's head, "There is no rush."

Philip sighed, "I don't know what to do."

"I can't make that decision for you," said Eliza, "You could always tell her that you like her."

"No!" Philip protested, eyes wide.

Eliza chuckled, "Whatever you decide to do."

A little while later Angie returned home from gymnastics, her hair was slipping from its braid and her hands and leotard were coated in chalk. Theo was quick to follow, "Angie wait!" she called.

Theodosia walked at a slightly slower pace behind the girls shaking her head.

"Mama, Philip!" Angie called, skidding to a stop at the kitchen table, "I did a back walkover today!"

"Me too!" added Theo.

"That's great," Eliza smiled, she couldn't help but notice that Philip looked a little bit like a deer in the headlights.

"Philip, did you hear?" Angie asked, tugging playfully at one of his curls.

Philip focused on his sister and have her a grin, "Yeah. That's awesome."

Angie gave her brother a brief hug before she and Theo dashed off again.

"I hope Angie didn't make you too crazy," Eliza smiled as she went to talk to Theodosia.

"She's a pleasure as always," Theodosia laughed.

"I know that Aaron and Alex are caught up with a case," continued Eliza, "Would you two like to stay for dinner?"

"Oh that would be great," Theodosia smiled, "and I'm sure Theo won't mind."

The two girls could be heard chattering loudly, joined by Junior's giggles.

"Hello Philip," Theodosia addressed the eldest Hamilton.

"H-hello Dr. Burr," Philip stammered.

"I heard that you're writing poetry now," said Theodosia kindly.

Philip nodded, "It's fun."

"I would love to hear some of your work some day," Theodosia smiled.

Before Philip could say anything else he could hear Angie calling for him from the other room. He slipped out and joined his sister.

Eliza looked over at Theodosia after Philip had left, "I think my son has a bit of a crush," she confided.

  
"On Theo?" Theodosia asked, "That is so adorable."

Eliza nodded, "He told me this afternoon."

"He is such a sweet boy," Theodosia smiled, "even though they are a little young I think they would be cute together."

"Don't go picking out wedding china yet," laughed Eliza, "You know how fickle boys can be at his age."

"Ah yes, the perils of youth," Theodosia sighed jokingly.

"To be young," Eliza smiled.

\----------

The next day, Philip was leaning up against the wall of the gym where they had recess every day.

He saw Theo and Angie across the gym as he debated what he was going to do, he considered taking his mother's words to heart and asking her but something kept stopping him.

The two girls were jumping rope, chatting and giggling together. Philip watched them for several moments, waving off one of his classmate's invitations to join in the heated game of Four Squared a lot of the boys were playing.

This shouldn't scare him so much, right? It was just Theo, that hadn't changed. She wasn't all of a sudden a different person, it didn't work that way.

He pushed himself to his feet and took a breath before beginning to stride to the opposite side of the gym, carefully dodging the second graders playing tag.

As he got closer the girl's stopped what they were doing and by some stroke of luck Angie went to go and get a drink of water leaving him alone with Theo.

"Hi Philip!" Theo smiled.

"Hey," Philip replied, stuffing his hands in his pocket nervously, "Um, can I ask you a question?"

"What is it?" chirped Theo.

"I uh.." Philip scratched at the back of his neck, Theodosia looked at him expectantly.

"I think I like you."

"I like you too!" Theo grinned.

Philip felt his heart soar, "Really? So, do you want to be my girlfriend?"

Theo cocked her head and frowned, "What?"

Philip felt his jaw drop and he felt his heart beating wildly in his chest, now what was he going to do?

"My friends dared me to ask you," Philip blurted out. It was the first thing that came to his mind. Thankfully, Theo just laughed.

"Boys are so weird."

Philip sighed and looked at his scuffed up shoes, deciding to walk away before his sister came back.

**Notes for the Chapter:**

> Ages:  
> Philip-11  
> Angie and Theo-9  
> Junior-7  
> James-5


	2. Attempt #2

It was late October and Philip had seen enough posters plastered in the hallway to remind him of the fact that there was indeed a Halloween dance. Now up until this point he had not given it much thought, but as it came closer and closer to the date he got an idea that he could not shake. Perhaps this was fate's way of telling him now was the time for him to try asking Theo out again... That is if she wasn't going with someone else. Thankfully there was someone who could provide him with the answer to that question.

"Hey Ange."

"What's up?" Angie asked as she pulled her hair out of the ponytail she had put her hair in for gymnastics.

"You know we've got that Halloween dance coming up at school-" 

"What about it?" Angie asked looking at the blisters she'd gotten from the uneven bars.

"I was just wondering," Philip hesitated, "do you know if Theo is going with anyone..." His voice started trail off during the later half of his sentence.

"Duh," Angie laughed, "Theo and I are going together, you should know that we're going as-" Angie stopped and her eyes grew wide, "Oh. My. God."

"What?" Philip raised his brow.

"You like her," Angie grinned.

Philip began to blush, "I don't know what you're talking about-"

"Admit it!" Angie giggled, "you like Theo!"

"Keep it down will you?" Philip huffed, "don't need to broadcast it to the world."

"So are you going to the dance with her?" Angie spoke only little quieter.

"You said you were going with her-"

"Don't you dare let that stop you!" Angie crossed her arms, "I can live without my best friend for one night."

"I suppose I could," Philip nodded, although he never could forget his truly disastrous attempt at trying tell Theo how he felt a few short years prior.

"It could be fun," Angie smiled, "and you better ask her soon."

"Why?" Philip asked worriedly, "Is someone else thinking of asking her."

Angie giggled.

"Costumes!" she declared as if it was the most obvious thing in in the world.

"But you said that-"

"Things change," Angie interrupted her brother.

Philip sighed.

"I'm giving you three days."

"What?" Philip looked at his sister.

"Three days," Angie repeated and held up three fingers, "or it's back to Theo and I going together."

"You can't rush these kinds of things," protested Philip.

Angie raised an eyebrow.

"Okay, well you shouldn't," Philip amended.

"Three days," Angie smirked.

Philip sighed knowing his sister really meant it.

The biggest problem ended up being finding a chance to talk to Theo by herself. They didn't interact much during school, since they were in different grades. The first day, Theo and Angie had gymnastics and Angie slept over at Theo's so Dr. Burr had driven them while Philip took the bus home. The second day, Philip had a student council meeting after school and by the time he has finished Theo was already gone.

So now it was day three, and Angie made sure he was very aware of this.

"You know what day it is, right?" Angie stood there as he exited the bathroom.

Philip resisted the urge to roll his eyes, "Yes."

It sounded confident, but Philip was anything but.

"Aaaaand," Angie stood in a way to make it impossible for him to pass.

"And," mumbled Philip, "if I don't ask Theo to the Halloween dance by the end of the day then..." he frowned, "Hang on, what could you even do if I don't ask her today?"

"Let's just say you don't want to know," Angie winked.

Philip huffed and pushed his way past her, ignoring the giggling that followed him down the hall.

Philip brushed it off, he could do this. He didn't need to worry about Angie's stupid deadline. In fact he knew he would succeed in asking Theo to the dance. Or at least that's what he had to keep telling himself.

He continued to tell himself that as he sat through his classes and as he passed by Theo in the hallway twice before lunch. He definitely wasn't chickening out in asking her. Definitely not.

So when lunch came around he was certain this was going to be it, he was going to ask Theo to the dance. They would have a great time, and they would--

"Hi Philip!"

Philip slowly turned around to see Theo and Angie standing right there, this is not what he had planned.

"Theo, Angie," Philip greeted, resisting the urge to duck away, especially because of the grin on his sister's face.

 

"Want to have lunch with us?"

Well Philip certainly could not say no to that, not with Angie standing right there.

"You guys go get a table," Angie said without waiting for Philip's response, "I need to talk to Mr. Griffith about my math test."

The two of them went in search of a table, Philip could hear his heart beating in his ears.

Theo watched her friend go before looking back at Philip, "Shall we?"

Philip nodded and they walked over to the line for food, he knew Angie had this all figured out because this left them ample time to chat while they waited.

"So Theo--" Philip began.

"Ooo! It's pizza day!" Theo exclaimed, grabbing a tray.

"Yay," Philip mumbled, taking a tray as well. Don't lose your nerve, he told himself sternly.

He reached for a tray as they continued to move down the line, "So I've been thinking about the Halloween dance."

"It's gonna be so much fun," Theo beamed.

"Er, yeah it will," agreed Philip as they inched along in the line, grabbing an apple.

Theo leaned across him to get the last pear, "I am so excited."

"Yeah," Philip inhaled, "I know you are going with Angie, right?"

Theo nodded.

"I hope it's not too late but I was thinking that maybe we--" Philip's voice caught in his throat.

"You should totally come with us!" Theo interrupted happily.

"Well, actually," Philip put in, but Theo didn't appear to hear him.

"We could all dress up together," she said, swiping her student card to pay for her meal.

"Uhhh..." Philip tried to find the right words, "Well I uhh..."

His head was completely devoid a any words right or wrong for this situation.

Theo started shooting out ideas for their costumes as the two of them made their way to a table on the far side of the cafeteria, one of the few that were still empty.

"Those all sound awesome" was all Philip managed to get out as they sat down, a few minutes later they were joined by Angie.

"So, what's going on?" she chirped, carefully placing her own tray in the table.

"Philip's going to come with us to the dance," replied Theo, "We need to rethink our costume ideas, make it a group thing."

Angie glanced over at Philip, one eyebrow raised, obviously ready to give him a glare. When she caught the badly hidden hangdog expression on his face she just sighed and nudged his foot with hers under the table, pressing against it in reassurance.

**Notes for the Chapter:**

> Ages:  
> Philip-13  
> Angie and Theo-11


	3. Attempt #3

**Summary for the Chapter:**

> Philip finds himself thoroughly wedged in the friendzone.

**Notes for the Chapter:**

> This is the same camp as in Summer Shenanigans.

It was the last day of the summer, and while most of the day had been spent with them packing and cleaning the cabins they now had a few free hours to say farewell to the camp they've called home for the last eight weeks. This, Philip had decided would be a good way of finally telling Theo he liked her. Perhaps they could even sit together during No Smoking, the slideshow that they showed at midnight.

He had just seen Angie and she'd informed him that Theo was doing some last minute packing in their cabin, winking knowingly at him when she sent him on his way.

So Philip turned and walked along the narrow dirt path to Cabin 20, through the screen door he saw Theo sitting on her bed holding a tie dye shirt in her hands. Above her was Angie's bunk that was loaded up with Angie's duffle bags.

Philip opened the door that groaned loudly as he did so, "Hey."

Theo straightened up, almost as if she had just come out of a trance, "You alright?" Philip asked.

Theo nodded, but it was slow and she wouldn't look Philip in the eye. Her fingers tightened around the tie dye shirt, which Philip recognized as one she had made back in the first year she and Angie had joined him at camp.

"You don't look it," Philip walked closer, "mind if I join you?"

"Sure," Theo muttered.

Philip sat gingerly beside her on the bunk, close enough that their arms were almost touching.

"What's going on?" he asked.

Theo just shrugged, still refusing to look at him.

"You aren't getting off that easy Burr," Philip teased, he then noticed Theo rubbing her eye.

He put his hand on her shoulder, "I'm sure whatever it is can't be that bad."

Maybe, he thought, she would feel better if he got her hyped up for No Smoking. Philip took a breath, preparing to ask her to go with him so they could sit together. That was practically the camp version of going out.

"I'm leaving," Theo burst out, "I mean, my family. Dad got a new job and we're moving so I won't be going to high school with you guys."

Then again maybe it could be that bad, a thought jumped into his head.

"Does Angie know?"

Theo shook her head, "I didn't want it looming over the summer."

That was not good at all, Angie would be heartbroken... Judging by the look on Theo's face she recognized this as well, "She's going to hate me for not saying anything."

"Angie could never hate you," Philip interrupted, "you know that... Besides we'll still have summers...Right?"

Theo sniffled slightly and Philip was stricken when he saw a couple tears roll down her cheek.

"Yeah," she confirmed in a watery voice.

Clearly in this moment Theo needed him as a friend, as much as he really wanted to tell her how he felt...This was obviously not the best time for him to do so.

"Will you help me tell her?" Theo looked at him with pleading eyes.

"Of course I will," agreed Philip readily. In all honesty, he would do anything she asked of him.

Theo threw her arms around him and squeezed tightly. Philip was still mostly facing forward, so Theo's face ended up buried in his shoulder.

He stayed with Theo like that for a moment, "I don't want to do this, I wish I could pretend this wasn't happening," she muttered.

"Hey, it's not the end of the world," Philip reminded her, "I mean, I'm sure you guys will still text every day and Skype is awesome."

Theo giggled, "Yeah, I guess."

After another long moment, she sighed and sat up.

"Thanks, Philip," Theo said softly, "For making me feel better."

She quickly pressed a kiss to his cheek, the way Angie often did, and shot to her feet. Philip's heart pounded in his chest.

"I guess we should go talk to Angie," Theo brushed her hair out of her face.

"R-right," Philip cleared his throat, trying to will the slight blush out of his cheeks, at least hoping that Theo didn't notice it.

Philip slowly rose to his feet and the two exited the cabin, Theo walking closer to him than she normally did.

He spied Angie walking across the lane and when she saw the two of them together there was an obvious glint of excitement in her eyes as she casually made her way over to them.

"So," Angie grinned, "did so miss out on anything exciting?"

"I need to tell you something," Theo said, her voice close to a mumble.

Angie's grin faded into a frown.

"What's up?"

Theo glanced at Philip and he gave her an encouraging nod.

"I..." Theo paused, she could feel the tears starting again and her throat tightened, "I'm moving back to New York." Her voice was quiet.

Angie didn't even hesitate before throwing her arms around Theo and squeezing her tightly. The movement dislodged Philip from his previous position at Theo's side. He decided to leave the two girls to it, beginning to walk towards the program office. Maybe there was something he could do to help prepare for the closing bonfire or slideshow... Something to distract him.

**Notes for the Chapter:**

> Ages:  
> Philip-15  
> Angie and Theo-13
> 
> For those of you who are confused... Burr became a senator the same time Alex became SoT in this AU. They moved to DC where Angie and Theo remained close friends, now the Burrs are going back to NYC.


	4. Attempt #4

Upon returning from camp Angie and Theo were doing their best to make use of the last couple of weeks they had before Theo moved. Philip did not want to encroach on that, after all Theo was Angie's best friend... But he desperately wanted to tell her how he felt at least.

"Are you going to tell her?" Angie stood in the doorway.

"What?" Philip looked up in confusion.

"Theo," Angie added, "please tell me you are finally going to tell her?"

"I want to..." Philip muttered.

"So do it," replied Angie in exasperation.

"It's not as easy as you're making it seem, you know."

"I don't know why you're making this so difficult." Angie came in and flopped on the bed.

"I'm making this difficult?"

"We've known Theo forever," Angie sighed, "what do you really think she's going to do to you?"

"Angie," Philip leaned back against the wall.

"I'm serious," Angie scooted closer to her brother, "Theo is moving, you should at least say something to her."

"What if she doesn't think of me that way?" asked Philip miserably, "With my luck, she'll tell me that she thinks of me as a brother."

"You think you're gonna be friend zoned?" Angie laughed.

"It could happen," Philip replied, "and it probably will."

"Philip," she said, shaking her head, "I know for a fact that Theo--"

"Kids!"

Angie's sentence was interrupted by their mother's call.

"Time to go."

Angie let out a huff as she followed her brother out of his room and joined their parents and siblings to go to the Burrs for a going away party.

She didn't have a chance to assure her brother that Theo returned his affections, something the other girl had confessed several weeks previously, as they were caught up in the insanity that was their family.

It was always hectic when trying to get the entire family to go anywhere with the large number of kids, then trying to make sure everyone was buckled and car seats set up properly. Hence why they were always out the door at least fifteen minutes early.

Alex got in on the driver's side as Eliza made sure William was fastened into his car seat while Philip took care of John.

Once everyone was buckled and car doors shut Alex started the car as they made the drive to the Burr's house.

Once they arrived and were welcomed in, with only minimal glaring between their father and Mr. Burr, Angie found herself being dragged to Theo's room.

Theo let out a sigh as she shut the door behind her, "This is stupid," she muttered, "moving, this whole party..."

"You're making it seem like we'll never see each other again and it's bumming me out," Angie informed her friend, even as she gave Theo a comforting hug.

"It feels like we won't," Theo sighed, "I'm going to miss you."

"It's not forever," Angie broke away.

"It had better not be forever," Theo brushed her hair from her face.

Angie tried to devise some sort of plan to try and get Philip and Theo to talk to each other. She didn't want her to go away without even knowing how her brother felt.

Something told her that Philip would never just come out and say it, so she needed to get them alone together.

"I think Philip's going to miss you too," Angie spoke up.

"Right," Theo scoffed.

"I'm serious!"

Oh dear god, were they really both so oblivious? This was nearly enough to make Angie want to scream.

A soft knock sounded at the door and Dr. Burr popped her head through.

"Theo, please don't close yourself in here all evening," she said with a small smile.

Theo looked like she might have been about to argue, but sighed instead, "Yeah."

The two girls went and joined the party, and Angie was finding it exceedingly difficult to get Philip and Theo alone... This is the last time she ever plays matchmaker she decided.

Not that Philip wasn't trying to do the same, but breaking away from the party was no easy task.

She and Angie were talking with some of the other adults and he couldn't help notice the sadness in Theo's smile. More than anything he wanted to tell her how he felt, how he'd felt this way for a really long time.

Eventually, things started winding down--which possibly had something to do with the "discussion" Philip's father was having with Theo's.

Philip watched as Angie grabbed Theo's hand and practically dragged her in his direction. His heart started to beat wildly with nerves as they approached.

"I've been hogging Theo all evening," Angie said once she was within earshot, "and I think you said you had something to say to her?"

"I don't know--" Philip began, but brought himself to a halt at Angie's raised eyebrow. It was eerily reminiscent of their mother.

Angie, who was still holding Theo's hand, took Philip's with her other and dragged them to the hallway that lead to the bedrooms, just out of sight of the living room. She left them there alone.

Theo began to giggle slightly, it's what tended to happen whenever she got nervous, "What was that all about?"

Philip flushed and looked away, rubbing the back of his neck in embarrassment, "Who knows what goes on in Angie's mind."

"It's one of the things I love about her," replied Theo with a smile.

Philip grinned back, "Yeah."

They simply smiled at each other for a long moment before looking away, both blushing rather furiously.

"So..." Philip began his voice caught in his throat, "Theo I--"

"Yes?"

"I wanted to tell you," Philip began with a sudden burst of courage.

"Philip, there you are."

Philip turned to see his father standing with his hands on his hips.

"We have to go," Alex told his son.

"I'll be right there."

Philip's heart was pounding in his chest when he turned back to Theo, the courage he had been feeling fading into the background.

"What did you want to tell me?" Theo asked, biting her lip.

"I just," Philip sighed, his shoulders slumping, "Good luck in New York."

Theo was crestfallen, but she plastered a fake smile on her face.

"Thanks."

As they two of them embraced, Theo let the smile drop and Philip cursed himself in his mind, letting his eyes close in frustration.

**Notes for the Chapter:**

> Ages:  
> Philip-15  
> Angie and Theo-13


	5. Success!

**Summary for the Chapter:**

> The moment you've all been waiting for.

Every Tuesday and Thursday, Philip was forced to sit through the math class he was required to take in order to graduate. There was definitely a reason why he was majoring in poetry writing and a love of Algebra wasn't it. The only reason he might need numbers in his life would be to count syllables for sonnets, so the fact that he had to take Algebra made no sense to him. That was probably why he had put off taking it until his junior year. There was one good part about taking that class: Theo.

During the fall semester, he had run into Theo one day at the student union building. He had barely recognized her under the heavy winter jacket and a new, stylish haircut but they had reconnected all the same. Unfortunately, their schedules did not come close to matching up, so he'd had to survive on the occasional meet up and a slew of text messages. This semester, however, the path that he had to take on the way to his math class crossed perfectly with Theo's as she left her biology class.

If they were lucky they tended to have a little time to talk, and after a few weeks of this Philip decided he was going to go for it. He was going to ask her out, for real this time. No chickening out, no interference from anyone else, he was going to ask her god damnit.

Of course he had gotten nothing but support from Angie during their weekly Skype sessions, suitably enthusiastic and slightly on the side of pressuring him. He was definitely ready now. Definitely.

His class ended a bit early and Philip was out of there like a shot, enjoying the crispness of the early spring breeze as he headed towards the area where he and Theo always met up.

She waved as she approached and Philip grinned.

"Hey Theo," Philip greeted when Theodosia reached him.

"Hi," She smiled back at him.

Philip's heart started beating rapidly in his chest, "So..."

Theo looked at him expectantly, Philip suddenly was at a loss. It was so frustrating that "Philip Hamilton smooth talker and ladykiller" never failed to leave him when Theo was involved.

"Yes?"

Philip snapped out of his daze, "So, how was your morning class?"

"Boring as hell," Theo said with a laugh, "I already did all of it in my AP Chemistry class last year, but the credit from that won't transfer so I'm kind of stuck. There's something else on your mind, though," she continued, "What is it?"

Fuck, how could she possibly know that? Philip shifted from one foot to the other and plastered on a smile, "You've got me there..." he laughed nervously.

Theo raised her brow, "Are you okay?"

Philip nodded his head, "Yeah."

"Okay," Theo said with incredulity, drawing the word out slightly, "Well, I need to get to class so--"

"Willyougooutwithme?"

Theo looked at him and blinked, "What was that?"

Philip could feel the color draining from his face and his throat turning into knots. He inhaled deeply trying to relax himself before asking again, "Will you..." he paused, "go out with me?" he waited to gauge her reaction.

"Are you serious?"

Uh oh... Did he just ruin everything about his friendship with Theo? Philip pushed his hair from his face and nodded in the affirmative.

Theo smiled, "Of course."

Now it was Philip's turn to look dumbstruck, "Wait, really?"

Theo giggled, "You asked, and I just said yes."

"Holy shit."

"Have you been planning this for awhile?" Theo asked.

Philip nodded, "I don't even want to say how long."

"Why, Philip Hamilton!" Theo laughed.

Philip blushed.

"Well I have a class in fifteen, as you know, but I'm free after that," Theo said with a soft smile, "we can get dinner?"

"Sure," Philip smiled as well.

"I'll meet you at Lerner Hall," Theo decided, naming the student union building, "Let's say five-thirty?"

"Sounds good," Philip grinned.

"I'm looking forward to it," Theo replied.

"Me too," Philip said, blushing again, "see you later."

"See ya."

Theo placed a hand briefly on Philip's shoulder before she continued on her way to class. Philip stood for one incredulous moment, twisting so that he could watch Theo leaving. His phone started buzzing, he pulled out of his pocket to see Angie's picture. He answered the call quickly, "Hey Ange-"

"Did you ask her? I want to know all about it!"

Philip's jaw dropped, "How can you possibly know about that?"

"My feminine instincts," Angie replied, "now tell me all about it! What did she say?"

"She said yes."

Philip had to hold the phone away from here as Angie screamed with excitement, he then heard another female voice in the background.

"Angie, what the hell?"

"I'm fine Claire," she explained to her roommate, "My brother just asked his crush on a date!"

"Whatever. Will you just keep it down. Geeze."

Philip heard Angie grumbling and the telltale sounds of her gathering some things and leaving the dorm room. She and her roommate hadn't really clicked and she was very much looking forward to getting a new one the following year.

"So when are you going out?" she asked.

"Later today after she's done with class," replied Philip, unable to keep a grin from spreading across his face.

"Oh my god, this is great."

Philip could practically feel Angie's excitement radiating through the phone.

"This is a cause for celebration!" Angie declared, "today should be recognized as a national holiday-"

"Angie..." Philip groaned.

"It's been ten years Philip," Angie exclaimed, "don't you think that's a little ridiculous?"

Philip began to blush and was thankful Angie was in Boston and couldn't see him, "Will you stop? I asked her, are you happy now?"

"It's about time," Angie laughed, "I've been shipping you two for years."

"I know," Philip sighed, "you've made that perfectly clear-"

"You have made my day," Angie sighed contentedly.

"You know Ange I would really love to continue this conversation but I have to go to class and I'm sure you're busy too-"

"What?" Angie replied, "oh no, don't you dare hang up on me Philip Hamilton!"

Philip tapped end knowing full well that he has never going to hear the end of this from Angie and he was going to have a whole slew of messages later.

This did nothing to help the little bit of concentration he had for math class, he basically had no hope in the possibility of paying attention today. His mind was elsewhere, and try as he might he could not focus on variables or functions. It was a huge struggle for him not to sink into writing soppy love poems for the whole lesson.

Even after he managed to get through math, he still had to wait another agonizing two hours before he was meant to meet Theo.

He had gone back to his dorm and figured just maybe he should put on something a little bit nicer if he and Theo were going out this evening. But the question was what? He opened his closet doors and looked inside all the while messing with his hair in an attempt to do something with it.

When his hair flopped down into his face again Philip let out a sigh, he pulled out a black button up shirt with a small white pattern on it. He traded his long sleeved thermal shirt out for than in an attempt to look a little more put together that he usually was.

He soon gave up trying to tame his hair and just pulled it into a half ponytail so that it was stay out of his eyes. Just as he had finished doing the last button of his shirt, Philip felt his phone ringing again. He answered without looking at he called ID.

"Hello?"

"Philip."

It was his mother. Philip felt a sudden rush of panic. He had set times for calling home and Eliza didn't usually call him outside those times. He was hit with the worry that something was wrong.

"Mom, what is it?" he asked in a rush, "Is everything okay?"

"Yes," Eliza laughed, "I was actually going to ask you the same thing."

Philip frowned in confusion, "What? Why?"

"Angie called me."

Philip let out a small groan and sank down into his bed. This was what he got for hanging up on his little sister.

"It's just a date, mom," said Philip.

"I don't think it can be considered 'just' anything when you've been waiting for it for so long," Eliza informed him mildly.

Philip sighed. Of course Angie had told her all about that.

"Mom," he groaned.’

"It's okay to be nervous," said Eliza, "I know I was when your father first took me out."

Philip couldn't help it, his curiosity got the better of him, "Really?"

Eliza chuckled, "Oh yes. Granted, it took him a few months to ask me out not ten years."

Philip felt himself blushing once again as his mother said that, "Oh."

"But that's alright," Eliza replied reassuringly, "you've asked her now, that's what matters."

Philip and all his siblings knew how their mother and father met, but now he had forgotten the fact that they had been friends for sometime before they had ever started dating.

"I'm nervous," Philip admitted after a moment of silence.

"Just be yourself. There's a reason why Theo agreed to this date and it's because she likes who you naturally are," reassured Eliza, "Be gentlemanly, but don't overdo it so you don't make her feel like you think she's weak."

"I would never--" Philip began, that was one of the things he loved about Theo was her independence. There was a reason that she and Angie had always gotten on so well.

"I know you mean well," Eliza continued, "anyway, thankfully this isn't a blind date-"

"That might be better than this..."

"Believe me it's not," Eliza laughed, "your Aunt Angelica set me and Aunt Peggy up on a number of blind dates... It was terrible, to put it mildly."

"I really want to know what happened," Philip said with a grin.

"You really don't," replied Eliza flatly, drawing an amused snort from her eldest son.

"Okay, now I'm even more curious," he told her.

"That is a story for another time."

"Mom, please?" Philip laughed.

"Another time," Eliza replied firmly.

"Alright," conceded Philip, "I have to leave pretty soon anyway."

Oh god, the nerves were back. Philip let out a shaky breath, tucking the phone between his ear and shoulder so that he could press his palms in his jeans to ground himself.

"Have a good time, Simba," Eliza said in a hushed tone. The use of his childhood nickname was remarkably helpful in calming him.

"I will," he said, "Love you, mom."

He ended the call and rose to his feet, tucking the phone in his pocket. With one last look in the mirror, Philip tugged on a light jacket.

"Okay," he said to himself with determination, "You can do this."

Philip reached Lerner Hall slightly early in his nervousness and found himself attempting to lean casually against a nearby tree while he waiting. The whole "casual" thing didn't work, especially when five thirty ticked by and there was no sign of Theo.

With each passing minute his nerves worsened, maybe she wasn't going to show? Perhaps she'd only said yes because she felt sorry for him and now he was going stand their looking like fool--

"Sorry I'm late," Theo came up to him.

Philip pulled out of his thoughts with a start, "Oh, hey Theo."

"Sorry," Theo said again, "We did dissection during bio lab and some idiot knocked into me and," she laughed, "Long story short, I needed to get the smell of formaldehyde off of me."

Philip noticed that her bobbed hair was still slightly damp at the roots and she smelled strongly of vanilla and honey, obviously from extremely recent contact with soap.

"That's alright," said Philip with a small smile.

Theo hesitated for a moment, "So where are we going?" she asked.

"So I umm..." Philip began to blush again, "you remember that place we used to go when our dad's won big cases?"

Theo's eyes lit up, "Oh my god, I haven't been there in forever!"

"A good choice, then," laughed Philip.

"Definitely," Theo confirmed, hooking her arm through his, "Lead the way."

Philip smiled as they walked off campus to the nearest subway station that would take them to Little Italy. Once there they went down Mulberry Street in search of the restaurant.

"I always liked going here," Philip smiled, "I feel like after a case like that was the only time our dad's were ever able to get along," he laughed.

"I think they like each other more than they let on," said Theo with a giggle, "My dad doesn't have any problems complementing yours when he want to."

"I think they'll both be civil to each other for our sakes."

"Does your dad know that you're taking me out?" Theo asked.

Philip shrugged, "Maybe? My mom knows, but that's because Angie told her."

"You told Angie," said Theo with an amused grin, "Of course you did."

"Like you didn't," Philip countered, bumping her shoulder lightly with his.

"Touché."

Philip looked up at the address printed on one of the awnings, "Oops."

"What is it?"

Philip bit his lower lip, "I think we went just a little too far," he turned around.

"That's what you get for being such a good conversationalist," teased Theo.

"You're very distracting," Philip returned.

"Is that so?"

He blushed and avoided her gaze, "Yes."

It was now Theo's turn to blush, "So you'd been planning this for awhile... How long has it been, a few weeks?"

"Here we are," Philip said as he held the restaurant door open for Theo, completely avoiding the question.

Theo went inside but his avoidance did not go unnoticed in the slightest, she would get her answer eventually.

They walked over to the hostess stand in order to be seated.

The hostess grabbed two menus and walked them back, "Right this way," she sat them in a small two topper in the corner.

The place hadn't really changed over the years and was still the same stereotypical Italian decoration, bordering on the kitschy, with white and red checked table clothes and the tabletop candle mounted in an old wine bottle.

Theo looked at the decor as well as the menu and laughed slightly, "This is all a little Lady and the Tramp."

"Does that make me Lady or the Tramp?" Philip asked.

"Your hair reminds me of Lady," teased Theo, "But I hate to disappoint you, I won't be pushing any meatballs with my nose."

"As long as I get my spaghetti kiss, I don't mind," Philip shot back, then flushed when he realized what he had just said and continued in a mumble, "I mean, if you want to. Kiss me, that is. You don't have to."

Theo let out a giggle, "We'll see how tonight goes."

Philip wrung his hands in his lap as he looked at the menu, "You remember all the faces Angie drew on the to go boxes?"

"How could I forget?" Theo giggled, "she was quite good at that."

"She had a different face for each person," Philip remembered, "Everyone always knew which box was theirs."

"Yours always had freckles," Theo nodded, "an accurate representation if I recall correctly."

Philip let out a laugh, "That always seems to be one of the first things people notice."

"I've always liked your eyes," Theo replied, she then stopped.

Philip had no idea what to say to that.

"Philip I haven't been completely honest," Theo sighed, "I've kinda had a crush on you for quite awhile."

Philip sighed, "You don't know how much of a relief that is."

"So tell me," she continued, "How long has it been for you?"

Philip was once again saved from answering by the arrival of their waiter. He hoped that after they ordered their meals, the conversation could be turned in a different direction.

"I'll have the Carbonara," Theo ordered as the waiter turned to Alex.

"What would you like?"

"Ummm... I'll have the Chicken Parmesan," Philip replied as the waiter wrote down their order, smiled and walked away.

"Back to the matter at hand," Theo said, giving Philip a slightly evil grin, "I'm dying to know how long you've been planning on asking me out."

Philip hesitated, embarrassed.

"Do you remember back in elementary school," he started finally, "when I asked you to be my girlfriend?"

"You told me it was a dare from your friends," she laughed, then paused and noted the look on Philip's face, "Wait, since then?"

Philip nodded miserably, resting his head in his hands. She was going to laugh at him, he could feel it.

"Yeah..." Philip confessed.

"I..." Theo knit her brow, "I don't know what to say... This whole time?"

"You can laugh," Philip mumbled, the heels of his hands pressing into his eyes, elbows resting on the table.

 Theo reached out and gently touched his forearm, "I think it's sweet."

"You do?"

Philip looked up, meeting Theo's gaze. She was smiling softly, her eyes crinkling in the corners.

"Yes," she responded, squeezing his arm slightly.

Philip smiled, "This just makes me feel stupid for not saying anything until now."

"But you said something," Theo reminded him.

"I'm going to be honest, Angie has been threatening to tell you for months," Philip laughed.

"Why am I not surprised," Theo shook her head.

They shared a grin. The tension seemed to be broken now and conversation flowed easily while they waited for their food to arrive.

"I'm so glad you did ask," Theo smiled as the waiter returned with their food, "I had been wanting to hang out with you more."

"Oh?" Philip smiled.

"You know we should really get Angie out here at some point," Theo mused.

"Then she'll never leave," Philip laughed, "although she really is enjoying Boston."

"I'm glad to hear it," Theo smiled as she started in on her pasta.

"Me too," Philip admitted.

The two of them enjoyed the rest of their meal and their conversation flitted from when topic to the other. Philip relaxed and found that he was really enjoying his time. But their check came all too soon and after paying they took the scenic route to campus by way of gelato.

"This is me," Theo stopped in front of the building.

Philip sighed, he really did not want this to end.

"This was fun," he said, smiling.

Theo smiled back, "Yeah, I enjoyed it."

Philip fidgeted slightly, unsure of what to say next.

"Do you," he paused, looking away and rubbing the back of his neck, "Do you want to do it again some time?"

Theo thought about it for a moment, "I would love to," she grinned, "just don't wait so long next time," she teased.

Philip blushed slightly at that but knew that she was joking.

He laughed lightly, "Right."

"Hey, Philip?"

"Yeah?"

Theo stepped forward and leaned up, pressing a soft kiss to Philip's lips. He breathed in sharply though his nose. When they parted, Theo looked up at him shyly.

"Good night."

Philip watched her back as she retreated into the dorm building, in his daze barely remembering to call a quiet "good night."

**Notes for the Chapter:**

> Ages:  
> Philip-20  
> Angie and Theo-18
> 
> Notes: Yes, Eliza's childhood nickname for Philip is Simba and for obvious reasons because it's frickin' adorable.


End file.
